Out of My Brother’s League
by Wine-into-Water
Summary: DeanJess The first time Dean meets Jess isn't in Sam's appartment.


**Title** – Out of My Brother's League  
**Rating** – PG15  
**Fandom** - Supernatural  
**Characters** – Dean Winchester and Jessica Moore  
**Warnings** – A couple bad words  
**Summary** – The first time Dean meets Jess, isn't in Sam's appartment  
**Authors Note** – This is my second stab at Supernatural fic. This wasn't what I set out to do, my plan was go go in a total different direction but this came out instead, hopefully I pulled it off. Any and all constructive criticism is welcomed.  
**AN2** – Inspired by faithinFaith….she knows which part.  
**Beta** - **sailorhathor** Thank you so much! Any and all mistakes left are mine.  
**Disclaimer** - Supernatural and all its characters belong to Eric Kripke and the WB/CW. No copyright infringement is intended, I only borrow them for my own enjoyment.

**Out of My Brother's League**

The first time he sees her…

It's half past nine and he's drunk. The worst kind of drunk - didn't take the first drink to wind down after a hunt or even to be sociable, took the first drink because he was feeling sorry for himself, wants to drown in a mixture of self pity and Jack Daniels.

It's the first birthday he can clearly remember without Sam. He's spent birthdays covered in blood and near death, spent one memorable birthday getting chased by a werewolf, but no matter what, Sammy was always around to remember, to be the only one sometimes to wish him a happy birthday. He's been waiting two fuckin' days in this shit-ass town for the call. Waited to hear Sam's voice on the other end of the line so he can say, "Guess what Sammy, I'm just down the street. Come meet me for a drink." But it's twenty to ten and he's given up on the call, orders another drink and thinks bitterly that he'll make it a point to miss Sammy's birthday this year.

The beer is cold when it lands on his chest.

"Oh god, I'm sorry. I'm such a klutz."

She's blushing and tucking a long strand of golden hair behind her ear as she reaches for a napkin.

He just watches her as she fumbles with the napkin, trying to dry off his beer-drenched shirt. She's his height, just a shave of difference, with long blond hair with curls and some frizz, but that's probably only because of the humidity outside. Big blue eyes that have a tint of mischief and a warm smile that contradicts the look in her eyes, makes her look sweet and innocent, but he has his doubts. He is, however, a hundred percent certain that it's not the booze talking when he thinks she's the prettiest girl he's ever met.

He buys her a drink because it's the least she can let him do after spilling hers all over him. She sits on the barstool beside him and crosses her legs, showing off more thigh than is really necessary, and Dean begins to wonder just who is picking up who here.

Another drink later and he finds out it's her birthday too, and that technically she's not old enough to be in the bar, but she used the money her folks sent her for her birthday to finally get a decent fake ID made. He's not supposed to tell anybody…it's a secret. She's going to Stanford, not because she wants to, but because her parents wanted her to. So she could be a doctor or lawyer or something else equally impressive in their social circle. What she really wants to be – well, she's not sure herself - but maybe she could be that girl in those music videos because she's got the legs for it, right? And really, who is Dean to argue? Oh, and her name is Jessica or Jess, doesn't really matter which one. Nobody ever calls her Jessie, though, and she's not sure why.

When Dean settles the tab and leads her out of the back of the bar, he pushes her against the cool brick wall as her mouth crashes against his and he's pulling up her skirt and she's fighting with his belt and jeans; soon she has her legs wrapped around his waist and the small of her back is being rubbed raw against the brick as he moves inside her. Dean calls her Jessie as he comes just because nobody ever calls her that, and she bites down hard on his neck, leaving her mark of approval.

He had only planned to drive her home, but she has this thing for his car, and who the fuck doesn't totally fall in love with a gorgeous blonde who can do things with her mouth that he's only read about in Penthouse "Forum" and who has a thing for his car? So they're on the hood of the Impala, tangled together and panting, trying to touch every inch of each other all at once. Dean's hoping to hell they're not leaving any dents when the theme song to "Thundercats" rings out from his phone. She pulls back enough so she can look him in the eyes and he only shrugs and says, "My little brother," before going back to sucking on her breast. Two minutes later his watch beeps, letting him know it's midnight.

The next two days are spent pretty much the same way. Just them sometimes talking, most of the time not, and Dean thinks for the first time in his life that he might want this for the long haul. Might want a girl like Jessie…no…might want Jessie to spend the rest of his life with, take a break from hunting, not quit all of it like Sammy did but just slow down a bit, hunt only on weekends or when it's something big. He thinks this could make him happy, knows it does make him happy. He's never had a hard-on for normal like Sam has, but he likes this, likes finding out some of Jessie's quirks, like singing the theme song to the "Smurfs" as she showers, and she can't fall asleep with him unless her feet are tangled with his because she knows they'll get cold later, and that will wake her up.

On the fourth morning, while she's still sleeping and Dean is on his way back to bed from the bathroom, his cell phone goes off, and his dad is saying it's important he gets to San Antonio as fast as he can. There is a poltergeist causing all sorts of trouble and it needs to be taken care of right away before anybody else gets hurt. Knows that Dean wanted to check on Sammy, but he's closer, so it makes more sense for him to go down there. So he kisses her good-bye without even knowing her fuckin' last name, leaves her a note saying he had to go, is brave enough to sign it _Love, Dean,_ and hopes she knows that she was more than just sex. Hopes she knows that he didn't wake her up because if she had asked him to stay, it would have been the first time he disobeyed his father since he was twelve.

The second time he sees her…

It's dark and Sam is helping him up off the floor. The lights come on and he hears her voice.

"Sam?"

There is a shiver that runs through his body, like he's just found out some really bad or good news. Dean's seen some shocking things in his life, but he never would have expected this when he broke into his little brother's apartment. It's really her. He's having trouble taking his eyes off of her; it's been far too long. She still has music video legs and her hair still falls down her back, blond and curly… eyes that sparkle and shine and a smile that almost stops his heart from beating.

"Dean, this is my girlfriend, Jessica."

And that hurts more than it ever should, but Jess_ie_ is smiling, and Sam just kinda fades to the background as he walks up to her, smiling too, letting her know without a doubt that he remembers her. Dean uses the shirt she's wearing to prove his point.

"I love the Smurfs." His grin growing wider as she gives him that look. "You're way out of my brother's league."

They both know it's true because Sammy doesn't date girls who fuck strangers in back alleys or on hoods of cars, doesn't date girls who spend the whole weekend with a guy and don't even think to get his last name. Sammy is a good boy. Dean and Jess, on the other hand, like things a bit more interesting.

She doesn't play along though, and he really didn't expect her to with Sam standing not even five feet away. She says something about putting something else on, and God, that is the last thing he wants her to do. She gives him that look, and he was wrong…should have known better; she is playing, and he's fighting the urge to grab her and take her right there against the wall or on the floor because it's not like they haven't tried both before, but he reminds himself that she's Sammy's now and that he did have a reason for coming here.

He walks back towards Sam as he talks to Jess. " I have to talk to your boyfriend about some private family business, but it was nice meeting you." And that sentence is loaded with hidden meaning that he hopes she gets…and damn it, he still doesn't know her last name. He'll ask Sam later.

Sam, the little shit, is wrapping his arm around her waist all possessive, like he knows about the weekend they spent together, like he's telling Dean not to even think about it. Just to prove his point, he tells Dean that anything he has to say can be said in front of Jess. Dean does get a little pleasure in only hearing Jessica or Jess come out of Sam's mouth and never Jessie.

_Actually, Sammy boy, there are things I can say to her that I can't say in front of **you**_, he thinks, but instead just says Dad is on a hunting trip and hasn't been home in a few days.

It's not long after that Sam is grabbing his coat and leading Dean to the front door. He looks back just once, while Sam is zipping up. Sees her smile at him as she tucks a strand of golden hair behind her ear, and she's still the most beautiful girl he's ever seen.

He thanks God that he doesn't see her the last time Sam does. Dean looks for her but there is too much smoke and flames to really see, but he knows she's there, sees the shape of her if nothing else. Feels awful for turning his back on her but needs to get Sammy out of there before he loses them both.

It's a week later. Sam is in the hotel room finally sleeping and Dean is sitting in his car, head held in his hands as tears find their way down his cheeks…because seriously, who the hell doesn't totally fall in love with a girl like Jessie?

The third time he sees her…

It's in a hotel room on the edge of some backwoods hick town in the middle of nowhere. Sam is out getting breakfast and Dean wakes up to find her watching him.

"Jessie?"

She smiles and tucks her hair behind her ear. He loves when she does that.

"Happy birthday."

He gets that shivery feeling all over again. He hadn't even thought about it until now, didn't even notice when he signed Johnny Burrows on the credit card receipt yesterday that it was dated January 23rd.

"Happy birthday," he whispers as a tear slides into his hair when he touches her.

She's on top of him and kissing him, her tongue tangling with his. Hands are roaming over familiar territory, breathing getting faster and need becoming more urgent. He thinks for a second that this is wrong, he shouldn't be thinking this or dreaming this or doing whatever the fuck this is; she's Sammy's girl.

She eases herself on to him, leans down and whispers, "I was your girl first." And they begin to move as one. Dean hasn't felt like this since the first night with her.

She's cuddling up to him, tucking her feet between his and resting her head against his chest, fingertips running idly over his abs.

"I've missed you Jessie."

He can feel her smile against his chest as she leaves a kiss over his heart.

"You're the only one who's ever called me that."

Dean is letting her hair slide through his fingers as he runs his hands through it.

"I know."

The door slams and he wakes up with a start.

"Sorry, didn't mean to wake you. The wind caught the door."

He's in bed alone and Sammy is handing him a coffee. It was only a dream…of course it was, because since when does a ghost take solid form just to have birthday sex with you? Not to mention said ghost was practically your brother's fiancé. Fuckin' dreams…he should really leave those up to Sam.

"Dean."

"Huh…what?"

"Your phone."

Dean listens to the strange sound coming from his phone.

Sam smiles. "Dude is that the Smurfs?"

He flips open the phone to see a text message.

_Happy B-day  
p.s. I was your grl 1st _


End file.
